diethyl (4S)-[3-O-acetyl-2-O-benzoyl-1-deoxy-1-(thymin-1-yl)-α-L-threofuranos-4-yl]phosphonate

Base Information

Chemical Name:diethyl (4S)-[3-O-acetyl-2-O-benzoyl-1-deoxy-1-(thymin-1-yl)-α-L-threofuranos-4-yl]phosphonate
CAS No.:1333476-33-7
Molecular Formula:C₂₂H₂₇N₂O₁₀P
Molecular Weight:510.438
Hs Code.:

Synonyms:diethyl (4S)-[3-O-acetyl-2-O-benzoyl-1-deoxy-1-(thymin-1-yl)-α-L-threofuranos-4-yl]phosphonate

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Chemical Property of diethyl (4S)-[3-O-acetyl-2-O-benzoyl-1-deoxy-1-(thymin-1-yl)-α-L-threofuranos-4-yl]phosphonate

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Technology Process of diethyl (4S)-[3-O-acetyl-2-O-benzoyl-1-deoxy-1-(thymin-1-yl)-α-L-threofuranos-4-yl]phosphonate

There total 8 articles about diethyl (4S)-[3-O-acetyl-2-O-benzoyl-1-deoxy-1-(thymin-1-yl)-α-L-threofuranos-4-yl]phosphonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 47.0%

: 1333476-31-5
diethyl (4S)-(1,3-di-O-acetyl-2-O-benzoyl-α-L-threofuranos-4-yl)phosphonate

: 116165-26-5
5-Methyl-1-trimethylsilanyl-1H-pyrimidine-2,4-dione

: 1333476-33-7
diethyl (4S)-[3-O-acetyl-2-O-benzoyl-1-deoxy-1-(thymin-1-yl)-α-L-threofuranos-4-yl]phosphonate

Guidance literature:: With tin(IV) chloride; In acetonitrile; at -10 - 20 ℃; Inert atmosphere;
DOI:10.1135/cccc2011038

Reference yield:

: C₂₂H₂₄O₆

: 1333476-33-7
diethyl (4S)-[3-O-acetyl-2-O-benzoyl-1-deoxy-1-(thymin-1-yl)-α-L-threofuranos-4-yl]phosphonate

Guidance literature:: Multi-step reaction with 7 steps

1: sodium methylate / methanol

2: pyridine; dicyclohexyl-carbodiimide; trifluoroacetic acid / dimethyl sulfoxide / 16 h / 20 °C

3: triethylamine / chloroform / 18 h / 0 °C

4: periodic acid dihydrate / 1,4-dioxane; water / 48 h / 50 °C / Darkness

5: dmap / pyridine / 0.5 h

6: chromium(VI) oxide; sodium periodate / tetrachloromethane; water; acetonitrile / 72 h / 20 °C / Darkness

7: tin(IV) chloride / acetonitrile / -10 - 20 °C / Inert atmosphere

With pyridine; chromium(VI) oxide; dmap; sodium periodate; periodic acid dihydrate; sodium methylate; tin(IV) chloride; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In 1,4-dioxane; pyridine; methanol; tetrachloromethane; chloroform; water; dimethyl sulfoxide; acetonitrile; 2: Moffat oxidation;
DOI:10.1135/cccc2011038

Reference yield:

: 1333476-29-1
diethyl (5S)-(3-O-benzyl-1,2-O-isopropylidene-α-L-xylofuranos-5-C-yl)phoshonate

: 1333476-33-7
diethyl (4S)-[3-O-acetyl-2-O-benzoyl-1-deoxy-1-(thymin-1-yl)-α-L-threofuranos-4-yl]phosphonate

Guidance literature:: Multi-step reaction with 4 steps

1: periodic acid dihydrate / 1,4-dioxane; water / 48 h / 50 °C / Darkness

2: dmap / pyridine / 0.5 h

3: chromium(VI) oxide; sodium periodate / tetrachloromethane; water; acetonitrile / 72 h / 20 °C / Darkness

4: tin(IV) chloride / acetonitrile / -10 - 20 °C / Inert atmosphere

With chromium(VI) oxide; dmap; sodium periodate; periodic acid dihydrate; tin(IV) chloride; In 1,4-dioxane; pyridine; tetrachloromethane; water; acetonitrile;
DOI:10.1135/cccc2011038